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Cookstown Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Cookstown vacation rentals

Interior

1. Clean & Cozy Home Near Downtown

Clean & Cozy Home Near Downtown
New Tecumseth
8.4 out of 10, Very good, (6 reviews)
"Very cozy stay for a weekend hockey tournament."
Canada
Suzanne
The price is AED 296
AED 696 total
includes taxes & fees
29 Sep - 30 Sep
Clean & Cozy Home Near Downtown
TV

2. Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful

Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
Bond head
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home and the host was very accommodating. One of the best places to stay in the area."
United States
A A.
The price is AED 392
AED 702 total
includes taxes & fees
8 Oct - 9 Oct
Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
TV, fireplace

3. The Chieftain Suite

The Chieftain Suite
Barrie
9.6 out of 10, Exceptional, (17 reviews)
"Very clean and quiet place to stay! Communication was great and I was able to check in an hour early."
Canada
Kaitlyn
The price is AED 286
AED 552 total
includes taxes & fees
29 Sep - 30 Sep
The Chieftain Suite
Smart TV

4. Crazy Farm C-Can Chalet

Crazy Farm C-Can Chalet
Innisfil
8.8 out of 10, Excellent, (6 reviews)
"Super cool rental, fun but also realistic and got the job done! Good location & felt safe! Would def stay again!"
Canada
Ashley
The price is AED 338
AED 464 total
includes taxes & fees
29 Sep - 30 Sep
Crazy Farm C-Can Chalet
Private kitchen

5. The Allandale Residence

The Allandale Residence
Barrie
9.8 out of 10, Exceptional, (17 reviews)
"Very nice place"
Canada
Melissa
The price is AED 390
AED 963 total
includes taxes & fees
29 Sep - 30 Sep
The Allandale Residence
Coffee/tea maker, fridge, microwave, oven

6. New, Clean and Comfortable Apartment with Private Entrance.

New, Clean and Comfortable Apartment with Private Entrance.
East Gwillimbury
9.0 out of 10, Wonderful, (12 reviews)
"easy to check in and a great place to stay! very helpful hosts."
United States
Kwame A.
The price is AED 374
AED 593 total
includes taxes & fees
29 Sep - 30 Sep
New, Clean and Comfortable Apartment with Private Entrance.
Exterior detail

7. The Luxe Haven

The Luxe Haven
East Gwillimbury
The price is AED 208
AED 904 total
includes taxes & fees
29 Sep - 30 Sep
The Luxe Haven
Exterior detail

8. Utopia villa and spa

Utopia villa and spa
Innisfil
10.0 out of 10, Exceptional, (11 reviews)
"The hosts were very accommodating and communication was good. The outside of the property is VERY deceiving but once inside it is beautiful and very cozy."
Canada
Krista K.
The price is AED 468
AED 1,356 total
includes taxes & fees
29 Sep - 30 Sep
Utopia villa and spa
Terrace/patio

9. Modern 4 Bedroom Townhouse in Barrie South

Modern 4 Bedroom Townhouse in Barrie South
Painswick
9.0 out of 10, Wonderful, (21 reviews)
"Was great!"
Canada
Patrick K.
The price is AED 361
AED 898 total
includes taxes & fees
5 Oct - 6 Oct
Modern 4 Bedroom Townhouse in Barrie South
Smart TV

10. Wonderful place of Lake Simkoe

Wonderful place of Lake Simkoe
Innisfil
8.8 out of 10, Excellent, (8 reviews)
"We only stayed 1 night but it was perfect "
Canada
William O.
The price is AED 351
AED 919 total
includes taxes & fees
30 Sep - 1 Oct
Wonderful place of Lake Simkoe
Exterior

11. Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower

Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
Sutton
9.6 out of 10, Exceptional, (156 reviews)
"Great get-away. The cabin was super relaxing and very private."
Canada
Jason
The price is AED 479
AED 858 total
includes taxes & fees
29 Sep - 30 Sep
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
Exterior

12. Stylish & Modern House ♥ Walking distance to Barrie Beach!

Stylish & Modern House ♥ Walking distance to Barrie Beach!
Barrie
6.0 out of 10, (1 review)
The price is AED 286
AED 699 total
includes taxes & fees
29 Sep - 30 Sep
Stylish & Modern House ♥ Walking distance to Barrie Beach!
Smart TV

13. Stunning 1BR w Pool ~ Free Parking & Self Check-In

Stunning 1BR w Pool ~ Free Parking & Self Check-In
Innisfil
10.0 out of 10, Exceptional, (3 reviews)
"This place was immaculate. Host was always super responsive. Had everything we needed. Highly recommend. We really enjoyed our stay."
Canada
Jennifer
The price is AED 377
AED 772 total
includes taxes & fees
5 Oct - 6 Oct
Stunning 1BR w Pool ~ Free Parking & Self Check-In
Terrace/patio

14. Peaceful Rejuvenessence Retreat w/ Spa-Inspired Amenities — Perfect Getaway!

Peaceful Rejuvenessence Retreat w/ Spa-Inspired Amenities — Perfect Getaway!
Georgina
10.0 out of 10, Exceptional, (1 review)
"The amenities of this property were amazing. The outdoor entertainment area with home theatre, hot tub, sauna and peaceful garden was fantastic It was a true gem, happy that I experienced with my family’s This is perfect for couple getaway or a girls trip! Highly recommend!"
Canada
Sorina
The price is AED 701
AED 933 total
includes taxes & fees
29 Sep - 30 Sep
Peaceful Rejuvenessence Retreat w/ Spa-Inspired Amenities — Perfect Getaway!
Interior

15. Spacious | Private | Quiet | 2 BR Walkout Suite

Spacious | Private | Quiet | 2 BR Walkout Suite
Aurora
10.0 out of 10, Exceptional, (1 review)
"This property is an amazing, family-friendly retreat located in a peaceful, quiet neighborhood. The spacious unit is impeccably clean and features a fully equipped kitchen. The host provides outstanding, responsive service, making this an ideal choice for both short-term and long-term stays. Highly recommended."
Canada
Ayla
The price is AED 257
AED 1,018 total
includes taxes & fees
29 Sep - 30 Sep
Spacious | Private | Quiet | 2 BR Walkout Suite
Interior

16. Bright 2 Bedroom Entire Basement Apartment

Bright 2 Bedroom Entire Basement Apartment
Angus
9.0 out of 10, Wonderful, (13 reviews)
"Great place"
United States
Adriano A.
The price is AED 294
AED 793 total
includes taxes & fees
4 Oct - 5 Oct
Bright 2 Bedroom Entire Basement Apartment
Coffee/tea maker, fridge, microwave, oven

17. West Oak @ Barrie H&ME Tech Build

West Oak @ Barrie H&ME Tech Build
Barrie
10.0 out of 10, Exceptional, (1 review)
"We had a group of five staying here, and it was great to have enough bedrooms and bathrooms for everyone. The house was clean, spacious, and comfortable. The owner was very responsive to our messages and answered all of our questions promptly. We would definitely look to book this house again, as it worked very well for our larger group and was conveniently located near the Barrie Ice Arena. Everyone had a great stay!"
United States
Rhea T.
The price is AED 701
AED 1,605 total
includes taxes & fees
29 Sep - 30 Sep
West Oak @ Barrie H&ME Tech Build
Private kitchen

18. Innisfil Getaway

Innisfil Getaway
Innisfil
The price is AED 647
AED 1,106 total
includes taxes & fees
29 Sep - 30 Sep
Innisfil Getaway
Coffee/tea maker, fridge, microwave, oven

19. Spacious 4 Bedroom House in Angus

Spacious 4 Bedroom House in Angus
Angus
9.2 out of 10, Wonderful, (9 reviews)
"Hassan was a fabulous host and the place was a great stay for our group! Would use again!"
Canada
Jesse
The price is AED 368
AED 906 total
includes taxes & fees
29 Sep - 30 Sep
Spacious 4 Bedroom House in Angus
WiFi, bed sheets

20. Peaceful Parkside End Unit | 3 Bedrooms | Sleeps 8

Peaceful Parkside End Unit | 3 Bedrooms | Sleeps 8
Ardagh Bluffs
The price is AED 468
AED 831 total
includes taxes & fees
30 Sep - 1 Oct
Peaceful Parkside End Unit | 3 Bedrooms | Sleeps 8
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cookstown Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"We enjoyed out stay and were pleasantly surprised when we got there to find out breakfast was included. Room was clean, staff were very nice and welcoming."
Brenda 1-night trip
Posted 2 hours ago
Quality Inn

Frequently asked questions

Are there vacation rentals in Cookstown?

Yes, you can find vacation rentals near the most popular attractions in Cookstown, or you can select a more remote option if you're looking for a relaxing stay. Cookstown is known for its golf courses and shopping.

What's the top vacation rental that Cookstown has to offer?

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!: This vacation home near Cookstown is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

What’s there to see and do in Cookstown?

Explore the area and family-friendly sights such as Splashon Water Park Barrie, or get out into nature at a spot like Holland Marsh. Tanger Outlets and Innisfil Creek Golf Course are other places to visit while you're in town.

What’s a vacation rental in Cookstown like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Cookstown. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.